As e-learning continues to evolve and become a mainstream offering in higher education, colleges and universities are faced with growing online enrollments and student demand for access to courses and programs delivered in an e-learning environment. In 2019, approximately one out of three students in the United States enrolled in at least one e-learning course. Higher education leaders at Historically Black Colleges and Universities (HBCUs) are driven to identify processes and models to support and sustain e-learning initiatives. The purpose of this collective case study is to investigate the involvement of administrative leadership and faculty in the development and sustainability of e-learning programs at three HBCUs. The research questions that guide this study include: How do the organizational structure and operations impact the development and sustainability of e-learning at HBCUs? What role do faculty play in the development of e-learning? What internal and external factors motivate HBCUs to embark on the development of an e-learning program? The use of semi- structured interviews and document analysis, framed by Marshall's (2011) eLearning Maturity Model, provided an understanding of the organizational capability of the participating organizations to support and sustain e-learning. Three major themes surfaced from the analysis of the data: (1) Resources and funding are needed to support e-learning, (2) A planning process should be in place to address e-learning across the campuses, and (3) Faculty have varying opinions of e-learning. Study findings provide a model for implementation and sustainability of e-learning at HBCUs and suggest that the planning process be inclusive of institutional stakeholders. The study substantiates the importance of faculty buy-in and participation in the planning and deployment of e-learning. Results from the study suggest implications and recommendations for leadership at HBCUs to understand, address, and support critical operational areas in order to build, enhance, scale, and sustain e-learning programs. Study findings contribute to the literature on e-learning implementation at HBCUs, specifically the role of faculty in the planning process. Finally, it is recommended that further research be conducted on the practicality of unifying e-learning operations under the direction of a leadership position responsible for championing e-learning across the institution. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]